The failure of the Bay of Pigs invasion in April 1961 was a disaster for the Kennedy administration. It made the young president look weak, and gave fuel to Cold Warriors in both parties who could not stand the presence of a Soviet-aligned, Communist dictatorship just ninety miles south of Florida.

Target: Fidel Castro
A couple of months later, a special investigation of the Bay of Pigs chaired by retired General Maxwell Taylor made its report. "There can be no long-term living with Castro," Taylor wrote, just in case President Kennedy was thinking of giving up. The president's brother -- the new point-man on the Cuba problem -- needed no such prompting. "We will take action against Castro," Bobby wrote. "It might be tomorrow, it might be in five days or ten days, or not for months. But it will come."

Nothing to Lose
Like most covert operations, the plan to oust the Cuban dictator was a slippery thing. Who was paid to do what to whom is still not clear. But one thing is certain: Robert Kennedy was in charge. Convinced he had been betrayed by his military and intelligence advisors in the decision to launch the Bay of Pigs invasion, John Kennedy placed Cuba in the hands of the one man he knew he could trust. But what could be done? At a White House meeting in November, 1961, RFK scribbled the following in his notes:

My idea is to stir things up on the island with espionage, sabotage, general disorder, run and operated by Cubans themselves with every group but Batistaites and Communists. Do not know if we will be successful in overthrowing Castro but we have nothing to lose in my estimate.

Top Priority
Pressure was on from both Democrats and Republicans to do something to undermine Castro. GOP leaders were constantly attacking the administration for "losing" Cuba by not providing air support for the Bay of Pigs invasion. Brushing aside a CIA National Intelligence Estimate which said that Castro enjoyed too much support in Cuba to be overthrown, Robert Kennedy organized a secret project, code named "Mongoose." On January 19, 1962, in a pep talk to the team, Kennedy called deposing Castro "the top priority of the U.S. government -- all else is secondary -- no time, money, effort, or manpower is to be spared."

The Game of Espionage
Small, covert, special operations -- not another large-scale military invasion -- would be the method this time. Kennedy's term of art was "counterinsurgency," also described as "social reform under pressure." He was so enamored of the fearless commandos and real-life James Bonds who did such work that he once invited Special Forces troops to Hickory Hill to instruct his children how to swing from trees.

Ops Mastermind
The man RFK chose to run the operation was legendary CIA operative Edward Lansdale, whose exploits fighting Communists in the Philippines in the 1950s made him a model for a character in Graham Greene's novel, The Quiet American. Playing on Kennedy's desperation and distaste for bureaucratic inertia, Landsdale hatched a series of operations which were to climax in a "Touchdown Play" by October 1962. Though highly skeptical in private, CIA Director Richard Helms spent around $100 million on manpower and equipment for a spy base in Miami. This did little, however, to address the fact that the Americans had very few "assets" left in Cuba, so tight was Castro's grip.

Plausibile Deniability
The CIA had been plotting to assassinate Castro since the summer of 1960, even before John Kennedy was elected. A congressional investigation of the CIA later uncovered eight separate plots of varying ridiculousness between 1960 and 1965. But did either John or Robert Kennedy actually order him killed? History will probably never know. The Kennedys knew the meaning of the term "plausible deniability" all too well, and had been taught the old Boston Irish political rule, "never write it down."

"Get Rid of Castro"
"Get rid of Castro and the Castro regime, quote-unquote." This is how Sam Halpern, executive officer of the CIA team charged with carrying out Operation Mongoose, described his orders from Director Helms. "And when I asked Dick, what does "Get rid of" mean, he said, 'Sam, use your imagination.' That was it... Now what does that mean, throw him in the ashcan? Kill him, or what? And nobody could tell me. Just get rid of. Remove him from power basically." Helms himself was responding to relentless pressure from the White House. "You haven't lived until you've had Bobby Kennedy rampant on your back," he later remarked.

The CIA and the Mob
The pressure was so great that it led to one of the most controversial and grotesque chapters in presidential history: the hiring of the Mafia to help assassinate Castro. Though the details are murky and RFK's involvement has never been proven, it went something like this. CIA operatives, aware that the Mob was eager to renew the profitable gambling business it enjoyed under the Batista regime, hired Mafia hitman Johnny Rosselli to kill Castro. If this wasn't sordid enough, FBI director J. Edgar Hoover learned of the plot from FBI surveillance of Mob boss Sam Giancana, who just happened to share a mistress with John Kennedy. These machinations have provided much of the fuel behind various conspiracy theories of John Kennedy's assassination in Dallas in 1963.

Who Knew?
It is unclear whether the Kennedys knew what was going on. There is evidence that John Kennedy opposed the assassination as policy. Bobby's biographer Evan Thomas concludes, "the Kennedys may have discussed the idea of assassination as a weapon of last resort. But they did not know the particulars of the Harvey-Rosselli operation -- or want to."

Bogged Down
Even with all the money and elaborate measures being thrown at the problem, removing Castro proved easier said than done. Thomas writes that "after seven months, Kennedy's secret war... was hopelessly bogged down, riven by personality clashes, incapable of producing the 'boom and bang' that Kennedy wanted to see on the island."

Pros and Cons
RFK continued to hector his team, questioning their efforts and proposing unworkable solutions of his own. While they humored him, most senior officials were resigned to failure. Some, like Secretary of State Dean Rusk, were afraid that too much "noise" in Cuba would complicate more important Cold War problems like the struggle over Berlin. National security advisor McGeorge Bundy thought the only options were another invasion -- which the president had ruled out -- and "learning to live with Castro." Only CIA director John McCone was on RFK's side, worried the Soviets would turn Cuba into a missile base.

On the Brink
Within weeks, McCone's fears were validated. Soviet premier Nikita Khrushchev, fearful of an American first strike, had ordered nuclear warheads to be slipped into Cuba as a deterrent. He also demanded that the American spy planes stop flying over his shipping -- which they agreed to do in early September. But in early October, at McCone's insistence, American U-2 flights resumed. And on October 16, RFK was called in to see some very disturbing pictures. The world stood on the brink of nuclear war.

A Shameful Legacy
Though it happened under the radar, history has revealed that Operation Mongoose was, in its own way, every bit as disastrous as the Bay of Pigs. "It was an expensive and embarrassing failure," summed up Thomas. "Castro after all is still alive in Cuba, and the people who tried to get him are long since gone. And the way they went after him, by hiring the Mafia, was something that has long-term effects on U.S. foreign policy. People still see the CIA as this sinister, nefarious force. It was a fundamentally foolish thing to do and Bobby bears real responsibility for it."